


Smile!

by merryghoul



Category: Gossip Girl
Genre: F/M
Language: English
Status: Completed
Published: 2011-01-25
Updated: 2011-01-25
Packaged: 2017-10-15 02:20:08
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,200
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/156016
Author URL: https://archiveofourown.org/users/merryghoul/pseuds/merryghoul
Summary: <blockquote class="userstuff">
              <p>Earlier in 2009, Chuck wanted to make a sex tape with Vanessa to hurt Nate and Blair.  He gets his wish later that year--the sex tape, at least.</p>
            </blockquote>





	Smile!

**Author's Note:**

  * For [Anonymous](https://archiveofourown.org/gifts?recipient=Anonymous).



> This was something I always had in mind for a gossipgirlanon prompt listed as "Chuck/Vanessa, sex tape." If I'm not mistaken the request was made before "Remains of the J," where Chuck did suggest he wanted to make a sex tape with Vanessa (Do the Gossip Girl writers lurk on kink comms? Or is it merely a Huge Fucking Hint about Ed and Jessica being in a relationship at the time?). The seconding request was made after "Remains of the J." For some reason, though, I envisioned it set in the episode "The Grandfather, Part II." I also see the uneven third season as a sandbox for kinky scenarios, especially between rare pairs/parings that don't get a lot of fanfic written about them (read: non "NJBC" parings).
> 
> The first part (March 2009) is set during "Remains of the J;" it's the scene where Vanessa comes to Chuck for help in getting Nate back from Blair, just before the immediate cut to black and the Gossip Girl "thump." The second part (November 2009) is set during "The Grandfather, Part II," and starts with the first scene in Chuck's penthouse. Then it goes AU.

**March 2009.**

Chuck slowly sipped his scotch.  The fire in the Van der Woodsens' fireplace was raging.

"How about..."  He licked his lips.  "You and I have sex.  We film it.  Someone 'steals' the tape and the video is 'leaked' onto PornHub.  I send a tip to Gossip Girl.  Nate--"

"No, Chuck.  I am not letting you film me so everyone on Gossip Girl will see my bare ass on a porn site."  Vanessa downed the scotch Chuck had poured for her and stared at him.

"Would you like another?"

"No."

Chuck looked up, his mouth slightly ajar.  He stroked his chin.    "How about...we go to Jenny's birthday party.  We have sex in my bedroom.  We film--"

" _No,_ Chuck.  No means no."  

Chuck looked down at the ground with a sullen face.

" _Okay,_ Chuck.  We go to Jenny's birthday party together.  We take a picture of us together at the party to make Nate and Blair jealous.  We send _that_ to Gossip Girl.  But no sex."

Chuck nodded.  "That sounds like a great idea."

"For someone who supposedly is the best schemer on the Upper East Side, you're the worst at planning."

"Well, I plan to fuck you one day.  I'm _well_ prepared for that."

Vanessa sighed.

 **November 2009.**

"...anything I could ever want, Nathaniel, I can have it at the touch of a button.  TiVo, Playstation 360, Blu-Ray--I don't have to lift a finger to get it."

Chuck and Nate stop in front of six security monitors, projected onto a flat screen television.

"This is the best part: security cameras hooked up to a DVR.  If someone tries to rob the Empire, I can stop watching my season pass of _Mad Men_ to discover the burglar."

"I thought you were going to talk about Blair," Nate asks, confused.

"What about her?"

Vanessa walks into Chuck's suite.  She is taping Nate's Van Der Bilt relatives--William, his grandfather; Tripp, his cousin; and Maureen, his cousin's wife--as they enter the suite.  

Chuck sees Vanessa enter the suite.  

"You know, talking about making sex tapes with Blair.  I thought that was your thing, Chuck."

"Nathaniel, we have _guests._  It would be rude to talk about my sex life in front of them."

Chuck greets the Van Der Bilts as Vanessa tapes them all from afar.  He keeps his eye on Vanessa.  Vanessa keeps his camera on him.  


  
***

  
Nate and the Van Der Bilts leave Chuck's suite together.  Vanessa films them all heading to Chuck's private elevator.  Chuck grabs her waist before she can get in with them.  

"Chuck."  She doesn't bother to look at him.  Her camera is focused on the elevator doors closing.

"It's not like your hands were free."

Vanessa breaks free of Chuck's grip.  She turns off her camera.

"Hey."  He purrs into Vanessa's right ear.  " We never made that sex tape."

"Chuck, I told you, a sex tape was never part of the deal."

"I wish it was.  I'm usually good at persuasion."

Chuck grinds his stiffening erection on Vanessa's ass.

"You're with _Blair_ now.  Why are you trying to put the moves on _me?_ "

Chuck takes a verbal pause.  "Blair doesn't have to know about this.  That is, unless you want me to leak the tape..."

"You're still disgusting."

"You always liked that about me."

Chuck spins Vanessa around.  The two of them begin to French-kiss near Chuck's elevator.  Chuck presses the call button.

They resume kissing until the elevator door opens.  Chuck pushes her inside.  The elevator doors shut.  Chuck pushes the emergency stop button.

As they kiss again Chuck pulls down her tights.  Vanessa turns the camera on Chuck as he rubs her inner thighs.  Chuck looks up at Vanessa and the camera.  "Is it on?"

"Yes, Chuck."  Vanessa is bored with him already.  

"Good.  Follow me."

Chuck's mouth zeroes in on Vanessa's clit.  He hoists Vanessa's left leg in the air and sucks and licks her clit furiously.  Vanessa films this as she is shaking and moaning.

"I've missed that rough tongue of yours."  She moans.

"Mmm-hmm," he hums.  

Chuck moves from Vanessa's clit to the entrance of her cunt.  He is able to taste her juices.  Slowly he puts her legs down.  A Magnum comes out of Chuck's pants.  He snorts.  "It's lubed.  It shouldn't hurt like the last time."

"I wasn't a virgin when I met you."  

"Then why were you... _oh._ "  

He motions for Vanessa to hand him the camera.  She obliges.  

"On the ground."

Vanessa carefully lies on the floor of the elevator, trying not to rip her leggings.  "At least I don't have to feel that Brillo pad of a chest of yours," she mumbles as she lies down.

Chuck lays the camera down in front of Vanessa, pushing it back so he can see himself and Vanessa in the camera's viewfinder.  He lifts her shirt up and takes the buttons off of his jacket, vest and shirt he is wearing.  He pulls down his pants and puts the Magnum on.

"Anything to please my lady."  He smirks. Vanessa groans.

Chuck furiously pumps into Vanessa as she uses her left hand to steady herself and her right to rub her clit.  Chuck is starting to sweat, to smell of sex; the smell as well as Chuck's pumping makes Vanessa roll her eyes in the back of her head.  She has the biggest, craziest smile on her face.  The sight and feel of Chuck's hairy chest isn't helping Vanessa not go crazy.  He sniffs.  "Are you wearing Daisy by Marc Jacobs?"

"Curve Kicks from a Target in Brooklyn."

"Figures."

The sex goes on for a few more minutes.  Sometimes Vanessa pumps alongside Chuck.  Sometimes she grips his jacket, her nails threatening to rip it to shreds.  Chuck's tongue is working overtime: he licks Vanessa's neck and breasts whenever he can get close to them.  At one point Chuck rubs the front of Vanessa's clit with his thumb while Vanessa rubs alongside her clit's length.  

Vanessa pulls Chuck closer to her as she comes, moaning loudly, quivering violently.  She smiles as she feels Chuck's not-a-Brillo Pad chest against hers.  Chuck takes a few more strokes inside of Vanessa before he pulls out.  The Magnum goes off of Chuck's dick and onto the elevator floor.  He pumps his dick and jizzes all over Vanessa's stomach, grunting as each bit of cum comes out.  When he finishes he collapses onto Vanessa, panting, smiling.

"We should do this more often."

"We're not doing this again, Chuck.  And you'll never see _this_  again, because I'm taping over this with footage of Tripp's campaign office as soon as possible."

***

  
Chuck is in his bathrobe.  Vanessa is in the shower, cleaning the cum and sweat off of her body.  Chuck has sent Vanessa's clothes to be laundered, to eliminate any possible evidence of him fucking Vanessa.  His own suit has been sent to the cleaners for the very same thing.  He changes the channel from Bloomberg Television to his own closed-circuit cameras.  He rewinds footage from an elevator in the Empire Hotel.

Chuck is pushing Vanessa into his elevator.  The elevator doors shut.  Chuck is pressing the emergency stop button.

Chuck strokes his cock. 


End file.
